38243-03-7 , (20R)-Ginsenoside Rg3
Cas:38243-03-7
C42H72O13 / 785.01
MFCD11045225
Ginsenosides are natural compounds found in the roots of the plant Panax ginseng. Ginsenosides have been shown to exhibit immune-enhancing properties and to potentiate the effects of radiation and cancer drugs. Ginsenosides are also known for their anti-inflammatory, analgesic, antipyretic, and vasodilatory effects. The most studied ginsenoside is Rg3. This compound has been shown to inhibit tumor growth by inhibiting collagen production, which is an important component of tumor cells. Rg3 also exhibits anticancer activity by enhancing the antitumor activity of other anticancer agents such as doxorubicin, etoposide, and cisplatin.
Natural triterpenoid saponin found in Panax notoginseng. Shows a variety of biological activities. Shows anti-tumor activity and suppresses COX-2 expression. Inhibits brain Na+ currents (IC50 = 32 μM). Modulatory role in neuroinflammation. Active in vivo and in vitro.
20(R)-Ginsenoside Rg3 is a saponin that has been found in P. ginseng and inhibits angiogenesis. 20(R)-Ginsenoside Rg3 (0.001-1 μM) dose-dependently reduces proliferation, capillary tube branching, and the expression of matrix metalloproteinase-9 (MMP-9) and MMP-2 in human umbilical vein endothelial cells (HUVECs). It reduces tumor cell invasion of MM1 rat hepatoma, B16FE7 mouse melanoma, OC-10 human lung carcinoma, and PSN-1 human pancreatic adenocarcinoma cells in vitro by 89, 73.7, 84.2, and 59.1%, respectively, when used at a concentration of 25 µM. However, it does not inhibit the proliferation of MM1 cells when used at concentrations ranging from 1.6 to 64 µM. 20(R)-Ginsenoside Rg3 (20 mg/kg) reduces tumor volume, increases the tumor necrosis rate by approximately 16%, and increases survival in a human Lewis lung carcinoma mouse xenograft model. It also reduces the total number of B16-BL6 melanoma cell and 26-M3.1 colon carcinoma cell lung colonies in mice by 27 and 51%, respectively, when administered at a dose of 100 µg. Topical administration of 20(R)-ginsenoside Rg3 (0.05% w/v) reduces ear thickness by 47.5% compared with control animals in a mouse model of oxazolone-induced contact dermatitis and reduces expression of COX-2, IL-4, IL-1, IFN, and TNF mRNA by greater than 25%.5
R-Ginsenodie Rg3 γ2 GABA-A receptor agonist, 7.1 K+ channel activator, α10 nAChR antagonist found in Panax. It exhibits a wide variety of biological activities, including decreasing expression of pro-inflammatory cytokines, reducing oxidative stress, and inhibiting tubular formation and migration of endothelial progenitor cells.
CAS Number | 38243-03-7 |
Product Name | (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(10R,12S,13R,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
IUPAC Name | (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(10R,12S,13R,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C42H72O13 |
Molecular Weight | 785 g/mol |
InChI | InChI=1S/C42H72O13/c1-21(2)10-9-15-41(7,51)27-13-17-40(6)22-11-12-26-38(3,4)29(14-16-39(26,5)23(22)18-28(45)42(27,40)8)54-37-35(33(49)31(47)25(20-44)53-37)55-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22?,23?,24-,25-,26?,27-,28+,29?,30-,31-,32+,33+,34-,35-,36+,37+,39-,40-,41-,42+/m1/s1 |
InChI Key | VOWJAFYNABYJKY-JLBFJOLRSA-N |
SMILES | CC(=CCCC(C)(C1CCC2(C1(C(CC3C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)O)C)C)O)C |
Solubility | Soluble in DMSO |
Canonical SMILES | CC(=CCCC(C)(C1CCC2(C1(C(CC3C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)O)C)C)O)C |
Isomeric SMILES | CC(=CCC[C@](C)([C@H]1CC[C@]2([C@@]1([C@H](CC3C2CCC4[C@@]3(CCC(C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)C)C)O)C |
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